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铜催化的C-X和C-H键的区域选择性裂解:一种二氧化硫固定策略。

Copper-Catalyzed Regioselective Cleavage of C-X and C-H Bonds: A Strategy for Sulfur Dioxide Fixation.

作者信息

Yang Daoshan, Sun Pengfei, Wei Wei, Liu Fengjuan, Zhang Hui, Wang Hua

机构信息

Institute of Medicine and Materials Applied Technologies, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, 273165, Shandong, P. R. China.

College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, P. R. China.

出版信息

Chemistry. 2018 Mar 20;24(17):4423-4427. doi: 10.1002/chem.201705866. Epub 2018 Feb 27.

DOI:10.1002/chem.201705866
PMID:29334420
Abstract

The first example of direct fixation of sulfur dioxide between heteroaryls and aryl halides has been developed via copper-catalyzed regioselective cleavage of C-X and C-H bonds under base-free and ligand-free conditions by using DABSO (1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide)) as a solid and bench-stable sulfur dioxide surrogate. This mild protocol results in double C-S bond-forming reactions from simple precursors in the absence of prefunctionalized organometallic reagents, arenediazonium salts, and iodonium salts which extends the still limited number of sulfur dioxide fixation strategies.

摘要

通过使用DABSO(1,4-二氮杂双环[2.2.2]辛烷双(二氧化硫))作为一种固态且易于储存的二氧化硫替代物,在无碱和无配体条件下,通过铜催化的C-X和C-H键的区域选择性裂解,首次实现了杂芳基与芳基卤化物之间直接固定二氧化硫。这种温和的方法在没有预官能化有机金属试剂、芳基重氮盐和碘鎓盐的情况下,从简单的前体生成了双C-S键形成反应,扩展了仍然有限的二氧化硫固定策略。

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